Private Investigator

  Most people just assume you're a bounty hunter, and... they're right, of sorts. You are a finder of lost or stolen things, valuable information, and yes, sometimes people. For the right price.

  You grew up in the middle classes of a large city. You learned to make friends where you found them and know that, while class has a lot to do with who you become, its not everything. You've seen nobles fall into petty thievery and gutter orphans rise to high ranking guards. And you, you are friends with both.

  You have contacts with in the town guard and the local thieves guild. And never does one jeopardize the other. You may take a commission from them from time to time but you don't "work" for them.

 Usually, the work is "my spouse has suddenly started keeping odd hours". Spoilers 9/10 times it's infidelity. Or the, "my 'priceless' pendant/ring/bracelet etc... is missing". Those are a little more fun and random. Could be genuinely stolen, or lost during a night of debauchery.   

 Sometimes and very rarely, its a kidnapping where the parents don't want their business spread across town. So subtly and discretion are best.

Skill Proficiencies: Choose two from among Deception, Insight, Persuasion, and Investigation

Tool Proficiencies: Choose two from among one type of gaming set, one musical instrument, and thieves’ tools

Languages: Because of your underworld connections you know thieves cant

Equipment: A set of clothes appropriate to your duties and a pouch containing 20 gp

Suggested Characteristics

Use the tables for the criminal background below as the basis for your bounty hunter’s traits and motivations, modifying the entries when appropriate to suit your identity as a bounty hunter.

For instance, your bond might involve other bounty hunters or the organizations or individuals that employ you. Your ideal could be associated with your determination always to catch your quarry or your desire to maintain your reputation for being dependable.

d8	Personality Trait
1	I always have a plan for what to do when things go wrong.
2	I am always calm, no matter what the situation. I never raise my voice or let my emotions control me.
3	The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden.
4	I would rather make a new friend than a new enemy.
5	I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
6	I don’t pay attention to the risks in a situation. Never tell me the odds.
7	The best way to get me to do something is to tell me I can’t do it.
8	I blow up at the slightest insult.

d6	Ideal
1	Honor. I don’t steal from others in the trade. (Lawful)
2	Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3	Charity. I steal from the wealthy so that I can help people in need. (Good)
4	Greed. I will do whatever it takes to become wealthy. (Evil)
5	People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down the Styx for all I care. (Neutral)
6	Redemption. There’s a spark of good in everyone. (Good)

d6	Bond
1	I’m trying to pay off an old debt I owe to a generous benefactor.
2	My ill-gotten gains go to support my family.
3	Something important was taken from me, and I aim to steal it back.
4	I will become the greatest thief that ever lived.
5	I’m guilty of a terrible crime. I hope I can redeem myself for it.
6	Someone I loved died because of a mistake I made. That will never happen again.

d6	Flaw
1	When I see something valuable, I can’t think about anything but how to steal it.
2	When faced with a choice between money and my friends, I usually choose the money.
3	If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
4	I have a “tell” that reveals when I’m lying.
5	I turn tail and run when things look bad.
6	An innocent person is in prison for a crime that I committed. I’m okay with that.